反应 #215755

反应方程式

sulfur dioxide

n-Butyllithium

sodium acetate trihydrate

hydroxylamine-O-sulfonic acid

product

2H-Thieno[3,2-e]-1,2,3-thiadiazine-1,1-dioxide

→

2H-Thieno[3,2-e]-1,2,3-thiadiazine-6-sulfonamide 1,1-dioxide

溶剂

water

—

hexanes

THF

反应条件

后处理

1. 1
   温度to warm to room temperature
2. 2
   其他Evaporation of the reaction mixture
3. 3
   其他provided a residue which
4. 4
   温度this solution was cooled to 0° C.
5. 5
   萃取The reaction mixture was extracted with ethyl acetate (2×5 mL)
6. 6
   干燥The combined extracts were dried over MgSO4
7. 7
   浓缩concentrated to a crude oil which
8. 8
   其他was purified by flash column chromatography (silica, hexane-ethyl acetate gradient)
9. 9
   其他to give a white solid
10. 10
    其他t>183° C

实验过程

The product from step B (0.1 g, 5.3 mmol) was dissolved in dry THF (4 mL) and cooled to -78° C. under nitrogen. n-Butyllithium (0.7 mL of a 2.5 M solution in hexanes, 1.75 mmol) was added dropwise, the mixture stirred for 1h at -78° C. A stream of sulfur dioxide gas was passed through the surface of the mixture for 15 min. and then the mixture was allowed to warm to room temperature. Evaporation of the reaction mixture provided a residue which was dissolved in water (5 mL) to which was added sodium acetate trihydrate (0.21 g, 1.39 mmol); this solution was cooled to 0° C. and hydroxylamine-O-sulfonic acid (0.18 g, 1.39 mmol) was added followed by stirring for 18 h. The reaction mixture was extracted with ethyl acetate (2×5 mL). The combined extracts were dried over MgSO4 and concentrated to a crude oil which was purified by flash column chromatography (silica, hexane-ethyl acetate gradient) to give a white solid. (0.021 g, 15%). decomposition:t>183° C. Cl-MS m/e 268 (m+H)+. 1HNMR (DMSO-d6): δ:7.90 (1H, 1s, CH); 8.22 (2H, S, NH2 exchangeable); 8.34 (1H, 1s, CH=N).

来源